#318 The Pivot — Randeep Singh Gill

When a slipped disc ends your dental career at its peak, what comes next? Randeep Singh Gill's story isn't about endings—it's about radical reinvention. 

A digital dentistry enthusiast whose career was built on precision and routine, Randeep found himself confronting an identity crisis when chronic neck pain forced him away from practice. But here's where it gets interesting: instead of retreating, he pivoted into the very thing he'd always loved but never pursued: technology. 

Now he's building Dental CFO, an AI-powered platform designed to give practice owners something he believes they desperately lack: clarity. From workaholic associate to tech founder, Randeep's journey exposes the fragility of our professional identities and the transferable skills we don't realise we possess until we're forced to use them.

In This Episode

00:04:10 - Why dentistry over computing

00:05:25 - Left hand, right hand

00:10:15 - Six-day weeks and holiday guilt

00:14:30 - When cutting down actually earned more

00:20:40 - Identity crisis and the grief of leaving

00:26:05 - Teaching himself AI and entrepreneurship

00:32:30 - The six-month online course

00:38:15 - Finding your niche: Cerec crowns and clarity

00:39:05 - Building Dental CFO for real-time intelligence

00:42:45 - Financial clarity as obsession

00:47:25 - LinkedIn and hundreds of conversations

01:03:30 - Blackbox thinking

01:13:30 - Mistakes in tech: ego and uncertainty

01:17:05 - Squad models and developer dynamics

01:20:10 - Missing the people and the routine

01:26:55 - AI anxiety and raising kids offline

01:29:40 - Competition nightmares in tech

01:35:00 - Fantasy dinner party

01:37:30 - Last days and legacy

About Randeep Singh Gill

Randeep qualified from King's College London in 2009 and spent over a decade as an associate, including 11.5 years at the same practice where he developed a passion for digital dentistry and same-day Cerec crowns. When a cervical disc injury cut his clinical career short, he retrained in AI and entrepreneurship, founding Dental CFO—a platform designed to give dental practice owners real-time financial intelligence and clarity.